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March 20, 2006 1:44 PM PST

Why Microsoft is no Craigslist

by Mike Yamamoto
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Microsoft is going after Craigslist for its classifed ads, and the New York Times wonders if the online community can survive the challenge. To which we ask: Why wouldn't it?

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It certainly isn't the first time that Craigslist has been in someone's crosshairs, and it certainly isn't the first time that Microsoft has tried its hand at this game. Classified ads--which for decades constituted more than 40 percent of the total advertising revenue for many daily newspapers--were a lucrative target of Microsoft's Sidewalk city guides in the late 1990s.

But that venture ended with Sidewalk being sold, and CEO Steve Ballmer said later that he would have kept Microsoft out of the media business if he could have done it all over again. Even if Microsoft does become a viable competitor to Craiglist with Windows Live Expo, ultimate success won't be easy. The wildfire popularity of Craigslist may have been a fluke, but that fluke now generates 3 billion page views a month--and, even more important, a kind of grassroots loyalty that few companies can replicate.

Blog community response:

"Even if Expo turns out to be cooler than Craigslist, it will be hard to wrest the millions of users from the anti-corporate site."
--MarketingShift

"Does anyone else think Craigslist is the ugliest site ever? I can't beleive a site that bad looking can become so big. Windows Live Expo has a Web 2.0 feel so right there its miles ahead of Craigslist in my book."
--Unhandled Perception

"I understand that not every product is able to compete with current widely-used Google online applications, but I think that if Microsoft integrates all the services into existing online applications it will be successful in several of these endeavors."
--Somewhat Frank

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